High-Throughput Photo- and Electrochemical sp2–sp3 Cross-Electrophile Coupling to Access Novel Tedizolid Analogs

The development of practical synthetic protocols integrating novel technologies may enable rapid and broad exploration of chemical space in medicinal chemistry campaigns. Cross-electrophile coupling (XEC) allows the diversification of an aromatic core with alkyl halides to increase the sp3 character...

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Bibliographic Details
Published in:ACS medicinal chemistry letters 2023-05, Vol.14 (5), p.666-671
Main Authors: Montero Bastidas, Jose Raul, L’Heureux, Scott, Liu, Wenbin, Lee, Ken, El Marrouni, Abdellatif
Format: Article
Language:English
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Summary:The development of practical synthetic protocols integrating novel technologies may enable rapid and broad exploration of chemical space in medicinal chemistry campaigns. Cross-electrophile coupling (XEC) allows the diversification of an aromatic core with alkyl halides to increase the sp3 character. Herein, we apply two alternative approaches via either photo- or electro-catalyzed XEC and showcase their complementarity to access novel tedizolid analogs. The parallel photochemical and electrochemical reactors with high light intensity and constant voltage respectively were chosen to yield good conversions, which allowed access to a wide range of derivatives in a much shorter time frame.
ISSN:1948-5875
1948-5875
DOI:10.1021/acsmedchemlett.2c00542